The objectives of the program include the synthesis of analogs of chorismate and prephenate and investigations of their activity as substrate inhibitors or suicide substrates for chorismate mutase or prephenate dehydrogenase. These target enzymes catalyze the biosynthesis of tyrosine and phenylalanine in bacteria, fungi, and higher plants. The long-range goal is the discovery of analogs that will be useful antibacterial agents and antifungal agents by selective blocking of target enzymes. Other objectives include the total synthesis of biosynthetic intermediates in chorismate pathway and the synthesis of substances that will be used for mechanistic investigations with chorismate mutase and prephenate dehydrogenase.